Azo compounds having unsubstituted or substituted 2-phenoxycarbonylethyl groups

ABSTRACT

Compounds of the formula ##STR1## wherein A is C 1-6  alkylene, D is a diazo component radical of the triazolyl, pyrazolyl, cyano(C 1-4  alkyl)-imidazolyl, 4-chlorothiazolyl, 4-chlorotheinyl-2, 3-phenyl-1,2,4-thiadiazolyl-5, isothiazolyl-5, benzoisothiazolyl-3 or 1,3,4-thiadiazolyl-5 series or the phenyl series wherein the phenyl group is free of sulfonyl groups and may be substituted, by a maximum of 3 substituents 5-nitrothiazolyl-2, ##STR2## R 1a  is phenyl or phenyl substituted by 1 to 4 substituents each of which is independently halo, C 1-4  alkyl, C 1-4  alkoxy, trifluoromethyl, hydroxy, nitro, formyl, cyano, --SCN, (C 1-4  alkyl)carbonyl, (C 1-4  alkyl)carbonylamino, (C 1-4  alkoxy)carbonyl, (C 1-4  alkyl)carbonyloxy, carbamoyl, (C 1-2  alkoxy)(C 2-3  alkoxy)carbonyl or phenyl, and 
     R 2  -R 4  and R 10  -R 15  are as defined in the specification, 
     and mixtures thereof, useful as disperse dyes particularly for dyeing and printing textile materials made of natural, synthetic or semi-synthetic hydrophobic organic materials.

This is a continuation of application Ser. No. 08.006,018, filed Jan.15, 1993 and now abandoned, which is a continuation-in-part of U.S.application Ser. No. 07/728,431, filed Jul. 11, 1991 and now, abandoned.

This invention relates to new disperse dyes.

According to the invention, there is provided compounds of formula I##STR3## wherein D is a diazo component radical of the triazolyl,pyrazolyl, cyano(C₁₋₄ alkyl)-imidazolyl, 4-chlorothiazolyl,4-chlorothienyl-2,3-phenyl-1,2,4-thiadiazolyl-5, isothiazolyl-5,benzoisothiazolyl-3 or 1,3,4-thiadiazolyl-5 series, the phenyl serieswherein the phenyl group is free of sulphonyl groups and may besubstituted by up to 3 substituents or the 5-nitrothiazolyl-2 series ora group of formula α, β or γ ##STR4## wherein R₁₀ is cyano, nitro, (C₁₋₄alkoxy)carbonyl, aminocarbonyl(carbamoyl), mono- or di-(C₁₋₄alkyl)aminocarbonyl or (C₁₋₄ alkyl)carbonyl,

R₁₁ is hydrogen, C₁₋₄ alkyl, phenyl or (C₁₋₄ alkyl)carbonyl,

R₁₂ is cyano, formyl, --CH═N--O(C₁₋₄ alkyl), nitro, phenylazo, (C₁₋₄-alkoxy)carbonyl, mono- or di-(C₁₋₄ alkyl)aminocarbonyl, aminosulphonyl(sulfamoyl), mono- or di-(C₁₋₄ alkyl)aminosulphonyl or (C₁₄alkyl)carbonyl,

R₁₃ is hydrogen, C₁₋₄ alkyl, halo or nitro,

R₁₄ is hydrogen, halo, C₁₋₄ alkoxy, cyano or nitro, and

R₁₅ is hydrogen, C₁₋₄ alkyl or phenyl;

R₁₅ is (C₁₋₆ alkylene)-CO--O--R_(1a), preferably (C₁₋₄alkylene)-CO--O--R_(1a), and more preferably CH₂ --CH₂ --CO--O--R_(1a) ;

wherein

R_(1a) is phenyl or phenyl substituted by 1 to 4 substituents each ofwhich is independently halo, C₁₋₄ alkyl, C₁₋₄ alkoxy, trifluoromethyl,hydroxy, nitro, formyl, cyano, --SCN, (C₁₋₄ alkyl)carbonyl, (C₁₋₄alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonyl, (C₁₋₄ alkyl)carbonyloxy,aminocarbonyl, (C₁₋₂ alkoxy)(C₂₋₃ alkoxy)carbonyl or phenyl;

R₂ is C₁₋₆ alkyl, C₂₋₆ alkenyl, halo(C₂₋₆ alkenyl), C₃₋₈ alkynyl,cyano(C₂₋₆ alkyl), benzyl, phenylethyl, phenylpropyl, hydroxy(C₁₋₆alkyl), (C₁₋₄ alkoxy)C₁₋₄ alkyl, (C₁₋₄ alkoxy)carbonyl(C₁₋₄ alkyl),(C₁₋₄)carbonyloxy(C₁₋₆ alkyl) or (C₁₋₄ alkoxy)carbonyloxy(C₁₋₄ alkyl)or, when D is a 2,4-dinitrophenyl group, unsubstituted or substituted inthe 5- and/or 6-position, or a heterocyclic group, then R₂ may also behydrogen,

R₄ is hydrogen, halo, C₁₋₄ alkoxy or (C₁₋₄ alkoxy)C₂₋₄ alkoxy, or

R₂ and R₄ taken together with the nitrogen atom and the carbon atom towhich they are respectively attached and the carbon atom connecting thesaid carbon and nitrogen atoms form a cyclic six-membered group, and

R₃ is hydrogen, halo, hydroxy or C₁₋₄ alkyl or, when D is2-cyano-4-nitrophenyl, a heterocyclic group or a trisubstituted phenylgroup, R₃ may also be formylamino (formamido), (C₁₋₃alkyl)carbonylamino, (C₂₋₃ alkenyl)carbonylamino, (C₁₋₄ alkoxy)(C₁₋₄alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonylamino or C₁₋₃alkylsulphonylamino; with the proviso that when D is2,5-dichloro-4-nitrophenyl, R₄ is hydrogen, R₁ is --CH₂ CH₂ --COOC₆ H₅and R₂ is --CH₂ CH₂ CN, then R₃ is not --NH--COCH₃.

When D is a diazo component radical of the thiadiazolyl-5 series, it ispreferably of the 3-phenyl-1,2,4-thiadiazolyl-5 series.

Any C₁₋₄ alkyl group is preferably ethyl or methyl and more preferablyis methyl. Any C₁₋₄ alkoxy group is preferably ethoxy or methoxy and ismore preferably methoxy. Each halo is independently fluoro, chloro,bromo or iodo, preferably fluoro, chloro or bromo and most preferablychloro or bromo. Any alkylene radical is linear or branched.

In R₁, the alkylene radical is more preferably A', where A' is --CH₂ CH₂--, --CH₂ CH₂ CH₂ --, ##STR5## and most preferably A' is --CH₂ --CH₂ --.

In R_(1a), any (C₁₋₂ alkoxy)(C₂₋₃ alkoxy)carbonyl is preferably 2- or3-(C₁₋₂ alkoxy)(C₂₋₃ alkoxy)carbonyl.

Preferably D is Da where Da is a diazo compound of the 4-chlorothiazolylseries, 4-chlorothienyl-2; or 5-nitrothiazolyl-2 series, or a group offormula a) below.

Preferably Da is a diazo component selected from 4-chlorothiazolyl,4-chlorothienyl-2 or 5-nitrothiazolyl or is a group of formula a) below.

Preferably R_(1a) is R_(1a) ' where R_(1a) ' is phenyl, unsubstituted orsubstituted by one to four substituents selected from C₁₋₄ alkyl, C₁₋₄alkoxy, (C₁₋₄ alkoxy)carbonyl, C₁₋₄ alkylcarbonyl and halogen and up toone phenyl group.

Preferably A' is A_(a) ', where A_(a) ' is --(CH₂)₂₋₃

Preferably D is D', where D' is selected from groups (a) to (h) ##STR6##or D' is a diazo component of the 5-nitrothiazolyl series; wherein

R₂₀ is hydrogen, C₁₋₄ alkyl, halo, --CO--O(C₁₋₄ alkyl), cyano or nitro,preferably cyano or nitro,

R₂₁ is halo, C₁₋₄ alkyl, nitro or phenylazo, preferably nitro,

R₂₂ is hydrogen, halo, cyano or (C₁₋₄ alkoxy)carbonyl, preferablyhydrogen, chloro, bromo or cyano,

R₂₃ is formyl, cyano, --CH═N--O(C₁₋₄ alkyl) or --CH═C(CN)R_(25a),wherein R_(25a) a is cyano or (C₁₋₄ alkoxy)carbonyl, and

R_(23a) is cyano, nitro or --CO--O(C₁₋₄ alkyl),

R₂₄ is (₁₋₄ alkoxy)carbonyl, nitro or cyano,

R₂₆ is cyano(C₁₋₄ alkyl) or phenyl,

R₂₇ is C₁₋₄ alkyl or cyano(C₁₋₄ alkyl), and

R₂₉ is C₁₋₄ alkyl or phenyl.

In R₂₁, the phenyl group may be substituted by 1 to 4, preferably notmore than 3, substituents each of which is independently C₁₋₄ alkyl,nitro, halo or C₁₋₄ alkoxy. D is most preferably D", where D" is 2cyano-4-nitrophenyl, 2,4-dinitro-6-bromophenyl,,2,6-dichloro-4-nitrophenyl or 2,4-dinitro-6-chlorophenyl.

Preferably, R₁ is R₁ ', where R₁ ' is a group of formula (j) ##STR7##wherein each R_(26a) is independently hydrogen, fluoro, chloro, (C₁₋₂alkoxy)carbonyl, methyl, methoxy or ethoxy,

R_(27a) is hydrogen, fluoro, chloro, bromo, methyl, methoxy, ethoxy,(C₁₋₂ alkoxy)carbonyl or phenyl, and

R₂₈ is hydrogen, methyl, methoxy or ethoxy.

Preferably, the phenyl ring of the group of formula (j) contains amaximum of three substituents, more preferably a maximum of twosubstituents.

Preferably, there are at least two carbon atoms between any oxygen atomin R₂ and the nitrogen atom to which R₂ is attached and no carbon atomof R₂ that is part of a double or triple bond is directly attached tothe nitrogen atom to which R₂ is attached. R₂ is more preferably R₂ ',where R₂ ' is methyl, ethyl, allyl, 2-methylallyl, chloroallyl,propynyl, (C₁₋₂ alkyl)carbonyloxyethyl or (C₁₋₂ alkoxy)carbonyloxyethyland most preferably methyl.

R₃ is preferably R₃ ', where R₃ ' is hydrogen, methyl or (C₁₋₂alkyl)carbonylamino, and more preferably R₃ ", where R₃ " is hydrogen ormethyl.

The C₁₋₄ alkoxy group of any (C₁₋₄ alkoxy)(C₂₋₄ alkoxy) group as R₄ ispreferably in other than the 1-position. R₄ is preferably R₄ ', where R₄' is hydrogen or C₁₋₄ alkoxy (preferably methoxy or ethoxy), and mostpreferably hydrogen.

When R₂ and R₄ are part of a six-membered heterocyclic ring, the ringpreferably contains no hetero atom other than the nitrogen atom to whichR₂ is attached and is unsubstituted or substituted by 1 to 4, morepreferably 1, 2 or 3, substituents each of which is independently C₁₋₂alkyl and most preferably methyl.

The preferred compounds of formula I are those wherein D is D', thealkylene radical in R₁ is A', R_(1a) ' is a phenyl or substituted phenylgroup as in formula (j), R₂ is R₂ ', R₃ is R₃ ', and R₄ is R₄ '. Thoseof this group wherein R₁ is a group of formula (j) are more preferred,with those of this group wherein D is D" being even more preferred. Thecompounds of formula I wherein D is D', R₁ is a group of formula (j) thephenyl ring of which has not more than three (more preferably not morethan two) substituents, R₂ is R₂ ', R₃ is R₃ ", and R₄ is hydrogen arealso more preferred, with those of this group wherein D is D" being mostpreferred.

Especially preferred compounds of formula I are of formulae Ia to Ic##STR8## wherein n is 0 or 1;

R₅₀ is C₁₋₄ alkyl;

R₅₁ is NO₂ or CN;

R₅₂ is halogen (preferably CI or Br) or CN;

R₅₃ is a significance of R₂ other than hydrogen; and

R₅₄ is C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkoxycarbonyl or C₁₋₄alkylcarbonyl.

The compounds of formula I can be synthesized by reacting a diazotizedamine of formula II

    D--NH.sub.2                                                (II)

with one mole of a compound of formula III per mole of the compound offormula II ##STR9## The compounds of formulae II and III are known orcan be synthesized from known compounds by known methods.

The compounds of formula I can be incorporated into dyeing preparationsby known methods, for example by milling in the presence of a dispersingagent and/or filler. The preparations can then be granulated (optionallyunder vacuum) by the use of a fluidized bed or by atomizing to form drypreparations. These dry preparations can then be dispersed in a littleor a lot of water to form short or long dyebaths for use in exhaustdyeing, padding or printing processes.

The compounds of formula I can be exhausted from an aqueous liquor ontotextile materials of natural, semi-synthetic or fully synthetichydrophobic, high molecular weight organic materials. In particular, thecompounds of formula I can be used to dye and print textile materials oflinear aromatic polyesters as well as of cellulose 21/2 acetate andcellulose triacetate.

Dyeing, printing and padding can be carried out by known methods, forexample as described in French Patent 1,445,371.

The dyeings that result from application of the compounds of formula Ihave good properties, for example good thermomigration, fastness, goodlight fastness, good thermofixation, good sublimation and goodblistering fastness properties as well as good wet fastness properties,especially using a permanent press machine. The compounds of formula Ihave good fastness properties, especially thermomigration properties(for example, in the Marks & Spencer's (M&S) C4A 60° C. Test).

The invention will now be illustrated by the following examples in whichall temperatures are in °C.

EXAMPLE 1

16.3 parts of 2-amino-5-nitrobenzonitrile are stirred into 100 parts ofcold sulfuric acid (93%) and then reacted at 0°-5° C. over 30 minuteswith 30 parts nitrosyl sulfuric acid (40%). The mixture is stirred for afurther 3 to 4 hours at 0°-5° C. and is poured while stirring well, ontoa mixture of 26.9 parts 3-(N-methyl-N-phenylamino)propionic acid2-methylphenyl ester, 100 parts glacial acetic acid, 2 parts ofamidosulfonic acid, 200 parts water and 500 parts ice. The resultingdyestuff is filtered, washed acid-free with water and dried under vacuumat 60° C.

The resulting dyestuff is of formula 1a ##STR10## and has a λ_(max). of532 nm. It dyes polyester fiber material a ruby-red tone. The dyeing hasexcellent fastness properties.

EXAMPLE 2

Example 1 is repeated except that the 26.9 parts of3-(N-methyl-N-phenylamino)propionic acid 2'-methylphenyl ester isreplaced by 29.9 parts 3-(N-ethyl-N-phenylamino)propionic acid2'-methoxyphenyl ester. The resulting dyestuff of formula 2a ##STR11##has a λ_(max). =of 535 nm. It dyes polyester fiber material abluish-ruby red tone. The dye has excellent fastness properties and isparticularly useful in the rapid dyeing process.

EXAMPLE 3

20.7 parts of 1-amino-2,6-dichloro-4-nitrobenzene is stirred into 100parts of sulfuric acid (93%) and reacted at 30° C. over 1 hour with 32parts nitrosylsulfuric acid (40%). The mixture is stirred for 2-3 hoursat 30-32° C. and the resulting diazonium salt solution is addeddrop-wise to a mixture to 28.5 parts 3-(N-methyI-N-phenylamino)propionicacid 4'-methoxyphenyl ester, 50 parts of glacial acetic acid, 20 partsof water, 300 parts ice and 0.5 parts amidosulfonic acid. The mixture isthen slowly diluted with 500 parts water. The resulting dyestuff isfiltered, washed acid free with water and dried under vacuum at 60° C.

The resulting dyestuff of formula 3a ##STR12## has a λ_(max). =439 nm.It dyes polyester fiber material a yellow-brown tone and is particularlyuseful for rapid dyeing. The resulting dyeings have excellent fastnessproperties.

EXAMPLE 4

4.1 parts 2-amino-4-chloro-5-formylthiazole are added to 50 parts of 85%phosphoric acid at -10° to -5° C. over 30 minutes and are then reactedwith 8 parts nitrosylsulfuric acid (40%). This is stirred for a further3-4 hours at -5° C. and then the resulting mixture is poured whilestirring well into a mixture of 7.9 parts of3-(N-ethyl-N-3'-methylphenylamino)propionic acid 3"-methoxyphenyl ester,50 parts glacial acetic acid, 20 parts water and 250 parts ice. Thismixture is then stirred for 30 minutes and diluted by the slow additionof 500 parts ice water. The resulting dyestuff is filtered, washedacid-free with water and dried under vacuum.

The resulting dyestuff of formula 4a ##STR13## has a λ_(max). =586 nm.It dyes polyester fiber material a bluish-violet tone, and the resultingdyeings have good fastness properties. The dye of formula 4a isparticularly useful for rapid dyeing.

EXAMPLE 5

14.5 parts of 2-amino-5-nitrothiazole are stirred into a mixture of 75parts of sulfuric acid (93%), 85 parts of glacial acetic acid and 15parts of propionic acid. This is then reacted at 0°-2° C. over 30minutes with 32 parts of nitrosylsulfuric acid (40%). This is stirredfor a further 1-2 hours at 0°-2° C. and then is poured while stirringslowly onto a mixture of 28.5 parts of3-(N-methyI-N-phenylamino)propionic acid 3'-methoxyphenyl ester, 50parts of glacial acetic acid, 20 parts of water, 300 parts of ice and0.5 parts of amidosulfonic acid. This mixture is then slowly dilutedwith about 500 parts of water. The resulting dyestuff is filtered,washed acid-free with water and added under vacuum at 60° C.

The resulting dyestuff is a compound of formula 5a ##STR14## and has aλ_(max). =584 nm. It dyes polyester fiber material a bluish-violet toneand the resulting dyeings have excellent fastness properties. The dye isparticularly useful for rapid dyeing.

EXAMPLE 6

19.6 parts of 1-amino-2-methoxycarbonyl-4-nitrobenzene are dissolved at60° C. in 70 parts of glacial acetic acid. The resulting solution ispoured while stirring well onto a mixture of 150 parts of ice and 30parts of hydrochloric acid (ca. 30%). To the resulting fine suspension,a solution of 7 parts of sodium nitrite in 100 parts of water is addeddrop-wise at 0-5° C. over 1 hour. This is then stirred for a further 3hours at 0-5° C. The resulting solution is then reacted with 0.5 partsamidosulfonic acid and then added drop-wise over 15-20 minutes to asolution of 28.5 parts 3-(N-methyI-N-phenylamino)propionic acid3'-methoxyphenyl ester in 50 parts of glacial acetic acid. Sodiumacetate is added to assist in completing the coupling reaction. Theresulting dyestuff is filtered, washed with water and dried undervacuum.

The resulting compound is of formula 6a ##STR15## and has a λ_(max).=493 nm. It dyes polyester fiber material a scarlet red tone with goodfastness properties. The dyestuff is particularly useful for rapiddyeing.

EXAMPLES 7-53

Compounds of the formula ##STR16## in which R₂ and R₂₉ are given inTable 1 below can be prepared from known compounds by a method analogousto that of Example 1.

                                      TABLE 1                                     __________________________________________________________________________    Example                          Nuance on                                    Number                                                                             R.sub.2     R.sub.29        polyester                                    __________________________________________________________________________     7   C.sub.2 H.sub.5                                                                            ##STR17##      rubine                                        8   CH.sub.3                                                                                   ##STR18##        "                                           9     "                                                                                        ##STR19##        "                                          10     "                                                                                        ##STR20##        "                                          11     "                                                                                        ##STR21##        "                                          12     "                                                                                        ##STR22##        "                                          13     "                                                                                        ##STR23##        "                                          14   C.sub.2 H.sub.5                                                                             "               "                                          15   CH.sub.3                                                                                   ##STR24##        "                                          16     "                                                                                        ##STR25##        "                                          17   C.sub.2 H.sub.5                                                                            ##STR26##        "                                          18   CH.sub.3      "               "                                          19   C.sub.2 H.sub.5                                                                            ##STR27##        "                                          20   CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                             ##STR28##      red.                                         21   CH.sub.2 CH.sub.2 OCOOC.sub.4 H.sub.9 n                                                     "               "                                          22   CH.sub.3                                                                                   ##STR29##      rubine                                       23   C.sub.2 H.sub.5                                                                             "             rubine                                       24   CH.sub.3                                                                                   ##STR30##        "                                          25     "                                                                                        ##STR31##        "                                          26   C.sub.2 H.sub.5                                                                            ##STR32##        "                                          27     "                                                                                        ##STR33##        "                                          28   CH.sub.3                                                                                   ##STR34##        "                                          29     "                                                                                        ##STR35##        "                                          30   CH.sub.3                                                                                   ##STR36##        "                                          31   C.sub.2 H.sub.5                                                                             "               "                                          32     "                                                                                        ##STR37##        "                                          33   CH.sub.3      "               "                                          34   CH.sub.3                                                                                   ##STR38##        "                                          35   C.sub.2 H.sub.5                                                                             "               "                                          36   CH.sub.3                                                                                   ##STR39##        "                                          37     "                                                                                        ##STR40##        "                                          38     "                                                                                        ##STR41##        "                                          39     "                                                                                        ##STR42##        "                                          40   C.sub.2 H.sub.5                                                                            ##STR43##        "                                          41   CH.sub.3                                                                                   ##STR44##      rubine                                       42     "                                                                                        ##STR45##        "                                          43     "                                                                                        ##STR46##        "                                          44     "                                                                                        ##STR47##        "                                          45   CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                             ##STR48##      red                                          46   CH.sub.3                                                                                   ##STR49##      rubine                                       47     "                                                                                        ##STR50##        "                                          48     "                                                                                        ##STR51##        "                                          49   C.sub.2 H.sub.5                                                                            ##STR52##        "                                          50   CH.sub.3                                                                                   ##STR53##        "                                          51     "                                                                                        ##STR54##        "                                          52     "                                                                                        ##STR55##        "                                          53     "                                                                                        ##STR56##        "                                          __________________________________________________________________________

EXAMPLES 54-151

Compounds of the formula ##STR57## in which the symbols are defined inTable 2 can be prepared from known compounds by a method analogous tothat of Example 1.

                                      TABLE 2                                     __________________________________________________________________________    Ex.                                                     Nuance on             #  DK             R.sub.2    R.sub.3  R.sub.4 R.sub.29  polyester             __________________________________________________________________________    54                                                                                ##STR58##                                                                                    ##STR59## NHCOCH.sub.3                                                                           OCH.sub.3                                                                             2-methoxyphenyl                                                                         navy blue             55   "            CH.sub.2 CHCHCl                                                                            "        "       "         "                   56                                                                                ##STR60##     CH.sub.2 CH.sub.3                                                                        H        H         "       scarlett              57                                                                                ##STR61##       "        H        H         "       violet                58                                                                                ##STR62##       "        H        H       3-methoxyphenyl                                                                           "                   59                                                                                ##STR63##       "        NHCOCH.sub.3                                                                           H       2-methoxyphenyl                                                                         reddish violet        60   "            CH.sub.3     "      H         "         "                   61                                                                                ##STR64##       "        H        H         "       yellow brown          62                                                                                ##STR65##     C.sub.2 H.sub.5                                                                          H        H       3-methoxyphenyl                                                                           "                   63                                                                                ##STR66##     C.sub.4 H.sub.9 n                                                                        CH.sub.3 H         "       red                   64   "            C.sub.3 H.sub.7 n                                                                          "      H       2-methoxy-phenyl                                                                          "                   65                                                                                ##STR67##                                                                                    ##STR68## NHCOCH.sub.3                                                                           OC.sub.2 H.sub.4 OCH.sub.3                                                            3-methylphenyl                                                                          navy blue             66   "            C.sub.2 H.sub.5                                                                          NHCHO      "     3-methoxyphenyl                                                                           "                   67                                                                                ##STR69##     CH.sub.3   CH.sub.3 H         "       bluish violet         68                                                                                ##STR70##     C.sub.2 H.sub.5                                                                            "      H         "       reddish blue          69   "            CH.sub.3     "      H       3-methylphenyl                                                                            "                   70                                                                                ##STR71##     C.sub.2 H.sub.5                                                                            "      H       2-methylphenyl                                                                          red                   71   "              "          "      H       2-methoxycarbonyl                                                                         "                                                                 phenyl                          72                                                                                ##STR72##       "          "      H       C.sub.6 H.sub.5                                                                           "                   73                                                                                ##STR73##     C.sub.2 H.sub.5                                                                            "      H       3-methoxyphenyl                                                                         bluish red            74   "            CH.sub.3     "      H       2-methoxyphenyl                                                                           "                   75                                                                                ##STR74##       "        H        H       4-acetylphenyl                                                                          yellow brown          76   "            C.sub.2 H.sub.5                                                                          H        H         "         "                   77   "            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                            H        H         "         "                   78                                                                                ##STR75##     CH.sub.3   NHCOCH.sub.3                                                                           OCH.sub.3                                                                             C.sub.6 H.sub.5                                                                         navy blue             79   "            C.sub.2 H.sub.5                                                                            "        "       "         "                   80   "            H.sub.2 CHCH.sub.2                                                                         "        "       "         "                   81   "            CH.sub.2 CHCHCl                                                                            "        "       "         "                   82   "              "          "        "     3-methoxyphenyl                                                                           "                   83                                                                                ##STR76##       "          "        "       "         "                   84   "            C.sub.2 H.sub.5                                                                          NHCOC.sub.2 H.sub.5                                                                      "     2-methoxyphenyl                                                                           "                   85                                                                                ##STR77##     C.sub.2 H.sub.5                                                                          NHCOCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                      2-methoxyphenyl                                                                         navy blue             86   "            CH.sub.3     "        "     3-methylphenyl                                                                            "                   87   "            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              "        "       "         "                   88   "              "          "      OCH.sub.3                                                                             2-methoxycarbonyl-                                                                        "                                                                 phenyl                          89   "                                                                                           ##STR78## NHCOC.sub.2 H.sub.5                                                                      "     4-actylphenyl                                                                             "                   90   "            C.sub.2 H.sub.5                                                                          NHCOCHCH.sub.2                                                                           "     4-methylphenyl                                                                            "                   91                                                                                ##STR79##                                                                                    ##STR80## NHCOCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                      3-methylphenyl                                                                            "                   92                                                                                ##STR81##       "          "        "       "         "                   93   "            C.sub.2 H.sub.5                                                                            "        "       "         "                   94   "            CH.sub.3     "        "     3-methoxyphenyl                                                                           "                   95   "            C.sub.2 H.sub.5                                                                            "      OCH.sub.3                                                                             2-methoxyphenyl                                                                           "                   96   "            CH.sub.2 CHCHCl                                                                            "      OC.sub.2 H.sub.5                                                                        "         "                   97                                                                                ##STR82##                                                                                    ##STR83## NHCOCH.sub.3                                                                             "                                                                                    ##STR84##                                                                              navy blue             98                                                                                ##STR85##     CH.sub.3   H        H       2-fluorophenyl                                                                          yellow brown          99   "              "        H        H       4-methoxycarbonyl-                                                                        "                                                                 phenyl                          100                                                                               ##STR86##     C.sub.2 H.sub.5                                                                          CH.sub.3 H                                                                                      ##STR87##                                                                              reddish blue          101                                                                               ##STR88##       "        H        H                                                                                      ##STR89##                                                                              yellow brown          102                                                                                "              "        H        H       2-methoxyphenyl                                                                           "                   103                                                                                "              "        H        H       4-methoxy-phenyl                                                                          "                   104                                                                                "            CH.sub.3   H        H       3-methoxy-phenyl                                                                          "                   105                                                                                "              "        H        H       2-methoxy-phenyl                                                                          "                   106                                                                               ##STR90##       "        H        H       4-methoxy-phenyl                                                                          "                   107                                                                                "              "        H        H       3-methoxy-phenyl                                                                          "                   108                                                                               ##STR91##     CH.sub.3   H        H       4-methoxyphenyl                                                                         yellow brown          109                                                                               ##STR92##       "        H        H         "         "                   110                                                                               ##STR93##       "        H        H         "         "                   111                                                                               ##STR94##                                                                                    ##STR95## NHCOCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                      3-methoxyphenyl                                                                         navy blue             112                                                                                "            C.sub.2 H.sub.5                                                                            "        "     2-methoxyphenyl                                                                           "                   113                                                                               ##STR96##     C.sub.2 H.sub.5                                                                          H        H         "       reddish blue          114                                                                                "              "        CH.sub.3 H       C.sub.6 H.sub.5                                                                           "                   115                                                                               ##STR97##     CH.sub.3     "      H       3-methoxyphenyl                                                                         violet                116                                                                                "            C.sub.2 H.sub.5                                                                            "      H       C.sub.6 H.sub.5                                                                           "                   117                                                                               ##STR98##       "        H        H         "       navy blue             118                                                                               ##STR99##     CH.sub.3   CH.sub.3 H       3-methylphenyl                                                                          navy blue             119                                                                               ##STR100##    CH.sub.2 CH.sub.2 OCH.sub.3                                                              H        H       4-chlorophenyl                                                                            "                   120                                                                                "              "        H        H       2-methoxyphenyl                                                                           "                   121                                                                               ##STR101##    C.sub.2 H.sub.5                                                                          H        H         "       red                   122                                                                                "            CH.sub.3   H        H       C.sub.6 H.sub.5                                                                           "                   123                                                                               ##STR102##      "        H        H       2-methoxyphenyl                                                                         red                   124                                                                                "              "        CH.sub.3 H       C.sub.6 H.sub.5                                                                           "                   125                                                                               ##STR103##    C.sub.2 H.sub.5                                                                          H        H         "       red                   126                                                                                "            CH.sub.2 CHCH.sub.2                                                                      H        H       2-methyl-phenyl                                                                           "                   127                                                                               ##STR104##    C.sub.2 H.sub.5                                                                          NHCOCH.sub.3                                                                           H       3-methoxyphenyl                                                                         blue                  128                                                                               ##STR105##      "          "      H       C.sub.6 H.sub.5                                                                         red                   129                                                                                "              "        NHCOCH.sub.2 OCH.sub.3                                                                 H       2-methoxyphenyl                                                                           "                   130                                                                               ##STR106##      "        NHSO.sub.2 CH.sub.3                                                                    H                                                                                      ##STR107##                                                                             red                   131                                                                                "            CH(CH.sub.3)CH.sub.2 CH.sub.3                                                              "      H       2-fluorophenyl                                                                            "                   132                                                                               ##STR108##    CH.sub.3   NHCOOCH.sub.3                                                                          H                                                                                      ##STR109##                                                                               "                   133                                                                               ##STR110##      "        NHCOCH.sub.3                                                                           OCH.sub.3                                                                             C.sub.6 H.sub.5                                                                         navy blue             134                                                                                "                                                                                           ##STR111##                                                                                "      OCH.sub.2 CH.sub.3                                                                    2-methoxyphenyl                                                                           "                   135                                                                                "            C.sub.2 H.sub.5                                                                            "      OCH.sub.3                                                                             C.sub.6 H.sub.5                                                                           "                   136                                                                               ##STR112##    CH.sub.2 CH.sub.2 OH                                                                     H        H         "         "                   137                                                                               ##STR113##    C.sub.2 H.sub.5                                                                          Cl       H         "       bluish rubine         138                                                                                "              "        NHCOCH.sub.3                                                                           H       2-methoxy-phenyl                                                                        reddish violet        139                                                                               ##STR114##    H            "      OCH.sub.3                                                                               "       navy blue             140                                                                               ##STR115##    H            "        "                                                                                    ##STR116##                                                                               "                   141                                                                                "              "        NHCOCH.sub.2 CH.sub.3                                                                  OC.sub.2 H.sub.5                                                                      C.sub.6 H.sub.5                                                                         blue                  142                                                                               ##STR117##    CH.sub.3   H        H       4-ethoxy-phenyl                                                                         yellow brown          143                                                                               ##STR118##      "        CH.sub.3 H       2-methoxy-phenyl                                                                        bluish violet         144                                                                                "            CH.sub.3   H        H       2-fluoro-phenyl                                                                         violet                145                                                                               ##STR119##      "        H        OCH.sub.3                                                                             3-nitro-phenyl                                                                          yellow brown          146                                                                                "              "        H        H       4-fluoro-phenyl                                                                           "                   147                                                                                "              "        H        H       2-fluoro-phenyl                                                                           "                   148                                                                               ##STR120##    CH.sub.2 CH.sub.2 OCOCH.sub.3                                                            NHCOCH.sub.3                                                                           OCH.sub.3                                                                             2-methoxy-phenyl                                                                        navy blue             149                                                                                "              "          "      OCH.sub.2 CH.sub.2                                                                    C.sub.6 H.sub.5                                                                           "                   150                                                                               ##STR121##    CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                             "      OCH.sub.3                                                                             2-methyl-phenyl                                                                           "                   151                                                                               ##STR122##                                                                                   ##STR123##                                                                              NHCOCH.sub.2 CH.sub.3                                                                    "     3-methoxy-phenyl                                                                          "                   __________________________________________________________________________

EXAMPLES 152-182

Compounds of the formula ##STR124## in which the symbols are defined inTable 3 can be made by a method analogous to any one of Examples 1-6from known compounds.

                                      TABLE 3                                     __________________________________________________________________________                                                       nuance                     Ex.                                                on     λmax                                                                   ·          #  D          R.sub.2 R.sub.3                                                                              R.sub.4                                                                            R.sub.100                                                                            A         polyester                                                                            nm                  __________________________________________________________________________    152                                                                               ##STR125##                                                                              CH.sub.3                                                                              H      H    H      CH.sub.2 CH.sub.2 CH.sub.2                                                              rubine 541                 153                                                                               ##STR126##                                                                                "     H      H    H        "       yellow                                                                               446wn               154                                                                                "          "     H      H    3-OCH.sub.3                                                                            "         "    446                 155                                                                               ##STR127##                                                                                "     H      H      "      "       rubine 541                 156                                                                                "          "     H      H      "                                                                                   ##STR128##                                                                               "                        157                                                                                "          "     H      H    2-OCH.sub.3                                                                           ##STR129##                                                                               "                        158                                                                                "          "     H      H    3-CH.sub.3                                                                           CH.sub.2 CH.sub.2 CH.sub.2                                                    CH.sub.2    "                        159                                                                               ##STR130##                                                                              C.sub.2 H.sub.5                                                                       CH.sub.3                                                                             H    2-OCH.sub.3                                                                            "       blue                       160                                                                                "          "       "    H    3-OCH.sub.3                                                                          CH.sub.2 CH.sub.2 CH.sub.2                                                                "                        161                                                                               ##STR131##                                                                                "       "    H      "      "       bluish violet              162                                                                                "          "     NHCOCH.sub.3                                                                         OCH.sub.3                                                                            "      "       blue                       163                                                                               ##STR132##                                                                               ##STR133##                                                                             "    OC.sub.2 H.sub.5                                                                     "      "       blue                       164                                                                                "        CH.sub.2 CHCHCl                                                                         "    OCH.sub.3                                                                            "      "         "                        165                                                                               ##STR134##                                                                              H       NHCOCH.sub.3                                                                         OC.sub.2 H.sub.5                                                                   4-OCH.sub.3                                                                          CH.sub.2 CH.sub.2                                                                       blue                       166                                                                                "        CH.sub.2 CCH                                                                            "      "    "      "         "                        167                                                                                "          "       "    OCH.sub.3                                                                          4-COOC.sub.2 H.sub.5                                                                   "         "                        168                                                                                "          "       "      "  4-COOCH.sub.3                                                                          "         "                        169                                                                               ##STR135##                                                                                "       "      "    "      "         "                        170                                                                               ##STR136##                                                                              C.sub.2 H.sub.5                                                                       CH.sub.3                                                                             H    3-CH.sub.3                                                                             "       reddish blue               171                                                                                "          "       "    H    2-OCH.sub.3                                                                            "         "                        172                                                                                "        CH.sub.3                                                                              H      H    3,4-di-CH.sub.3                                                                        "       violet                     173                                                                                "        C.sub.2 H.sub.5                                                                       CH.sub.3                                                                             H    3-OCH.sub.3                                                                            "       reddish blue               174                                                                                "        CH.sub.3                                                                                "    OCH.sub.3                                                                          2-CH.sub.3                                                                             "       blue                       175                                                                               ##STR137##                                                                                "     H      H    3-OCH.sub.3                                                                            "       violet                     176                                                                                "        C.sub.2 H.sub.5                                                                       CH.sub.3                                                                             H    2-OCH.sub.3                                                                            "         "                        177                                                                                "        H       NHCOCH.sub.3                                                                         OCH.sub.3                                                                          3-CH.sub.3                                                                             "         "                        178                                                                                "                                                                                       ##STR138##                                                                             "      "    "      "       blue                       179                                                                                "          "       "    OC.sub.2 H.sub.5                                                                   4-OCH.sub.3                                                                            "         "                        180                                                                                "        C.sub.2 H.sub.5                                                                       CH.sub.3                                                                             H    3-CH.sub.3                                                                             "       violet                     181                                                                                "                                                                                       ##STR139##                                                                           NHCOCH.sub.3                                                                         OCH.sub.3                                                                          4-OCH.sub.3                                                                            "       blue                       182                                                                                "          "       "      "  4-OC.sub.2 H.sub.5                                                                     "         "                        __________________________________________________________________________

Examples 183-190

Compounds of the formula ##STR140## in which the symbols are defined inTable 4 below can be prepared from known compounds by a method analogousto any one of Example 1-6.

                                      TABLE 4                                     __________________________________________________________________________                                      Nuance on                                   Ex. #                                                                             D          R.sub.3   R.sub.101                                                                              polyester                                   __________________________________________________________________________    183                                                                                ##STR141##                                                                              CH.sub.3  3-methoxy-phenyl                                                                       blue                                        184   "        NHCOCH.sub.3                                                                            2-methoxy-phenyl                                                                         "                                         185   "          "       C.sub.6 H.sub.5                                                                          "                                         186                                                                                ##STR142##                                                                                "         "        "                                         187   "          "       2-methoxy-                                                                               "                                                                  carbonylphenyl                                       188   "        CH.sub.3  2-methoxy-phenyl                                                                         "                                         189                                                                                ##STR143##                                                                                "         "        "                                         190   "        NHCOCHCH.sub.2                                                                          4-fluoro-phenyl                                                                          "                                         __________________________________________________________________________

EXAMPLE 191

16.3 parts of 2-amino-5-nitrobenzonitrile are stirred into 100 parts ofcold sulphuric acid (93%) and are then reacted at 0-5° C. over 30minutes with 32 parts of nitrosylsulphuric acid (40%). This is stirredfor 3 to 4 hours at 0-5° C. and this is then poured into a mxiture of13.5 parts of 3-(N-methyI-N-phenylamino)propionic acid 2'-methylphenylester, 13.5 of 3-(N-methyI-N-phenyl-amino)propionic acid 4'-methylphenylester, 100 parts of glacial acetic acid, 2 parts of amidosulphonic acid,200 parts of water and 500 parts of ice. Coupling is terminated byadding sodium acetate. The resulting dyestuff is filtered, washed withwater and vacuum dried at 60° C. The resulting mixture comprises a 1:1mixture of the compounds of the formulae ##STR144##

This mixture dyes polyester fiber material a rubine-red tone and isparticularly suitable for rapid dyeing (for example, in the Foron® RDprocess). The dyeings have good fastness properties.

EXAMPLE 192

Example 191 is repeated replacing 13.5 parts of3-(N-methyI-N-phenyl-amino)propionic acid 2'-methylphenylester with 13.5parts of 3-(N-methyI-N-phenylamino)propionic acid-3'-methyl-phenylester. The resulting precipitate is a 50:50 mix of the compounds of theformulae below ##STR145##

This mixture dyes polyester fiber material a rubine-red tone and isparticularly useful in rapid dyeing. The resulting dyeings have goodfastness properties.

EXAMPLES 193-575

Compound of the formula ##STR146## in which the symbols are defined inTable 5 below can be made from known compounds by a method analogous tothat of Example 1.

    __________________________________________________________________________    Ex                                                       nuance on            #  DK           R.sub.2      R.sub.3    R.sub.4                                                                              R.sub.29  polyester            __________________________________________________________________________    193                                                                               ##STR147##                                                                                 ##STR148##  NHCOCH.sub.3                                                                             OCH.sub.3                                                                             ##STR149##                                                                             navy blue            194                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         195                                                                                "            "            "        OCH.sub.2 CH.sub.3                                                                   4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         196                                                                                "            "          NHCOCH.sub.3                                                                               "    4-ethoxy-carbonyl-                                                                        "                                                                 phenyl                         197                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxy-carbonyl-                                                                        "                                                                 phenyl                         198                                                                                "            "            "          "    3-methoxy-phenyl                                                                          "                  199                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  200                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  201                                                                                "            "            "        OCH.sub.3                                                                              "         "                  202                                                                                "            "            "          "    3-methyl-phenyl                                                                           "                  203                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  204                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  205                                                                                "            "            "        OCH.sub.3                                                                              "         "                  206                                                                                "            "            "        OC.sub.2 H.sub.4 CH.sub.3                                                            phenyl      "                  207                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  208                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  209                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  210                                                                                "          CH.sub.2 CHCH.sub.2                                                                        NHCOCH.sub.3                                                                             OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         211                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         212                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         213                                                                                "            "            "        OCH.sub.3                                                                            4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         214                                                                                "            "            "          "    4-aethoxy-carbonyl                                                                        "                                                                 phenyl                         215                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-aethoxy-carbonyl-                                                                       "                                                                 phenyl                         216                                                                                "            "          NHCOCH.sub.3                                                                               "    4-aethoxy-carbonyl-                                                                       "                                                                 phenyl                         217                                                                                "            "            "        OCH.sub.3                                                                            4-aethoxy-carbonyl-                                                                       "                                                                 phenyl                         218                                                                                "            "            "          "    3-methoxy-phenyl                                                                          "                  219                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  220                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  221                                                                                "            "            "        OCH.sub.3                                                                              "         "                  222                                                                                "            "            "          "    3-methyl-phenyl                                                                           "                  223                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  224                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  225                                                                                "            "            "        OCH.sub.3                                                                              "         "                  226                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      "      phenyl      "                  227                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  228                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  229                                                                                "          CH.sub.2 CHCHCl                                                                              "        OCH.sub.3                                                                            4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         230                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         231                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         232                                                                                "            "            "        OCH.sub.3                                                                            4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         233                                                                                "            "          NHCOCH.sub.3                                                                               "    4-ethoxy-carbonyl-                                                                        "                                                                 phenyl                         234                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxy-carbonyl-                                                                        "                                                                 phenyl                         235                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-ethoxy-carbonyl-                                                                        "                                                                 phenyl                         236                                                                                "            "            "          "    4-ethoxy-carbonyl-                                                                        "                                                                 phenyl                         237                                                                                "            "            "          "    3-methoxy-phenyl                                                                          "                  238                                                                                "            "            "        OCH.sub.3                                                                              "         "                  239                                                                                "            "          NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       "         "                  240                                                                                "            "                                                                                         ##STR150##                                                                                "      "         "                  241                                                                                "            "            "        OCH.sub.3                                                                              "         "                  242                                                                                "            "            "          "    3-methyl-phenyl                                                                           "                  243                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  244                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  245                                                                                "            "            "        OCH.sub.3                                                                              "         "                  246                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  247                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  248                                                                                "            "            "          "    phenyl      "                  249                                                                                "            "            "        OCH.sub.3                                                                              "         "                  250                                                                                "            "          NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       "         "                  251                                                                                "          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                "          "    4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         252                                                                                "            "            "        OCH.sub.3                                                                            4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         253                                                                                "            "                                                                                         ##STR151##                                                                              OC.sub.2 H.sub.5                                                                      ##STR152##                                                                               "                  254                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         255                                                                                "            "            "        OCH.sub.3                                                                            4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         256                                                                                "            "          NHCOCH.sub.3                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                           4-methoxy-carbonyl-                                                                       "                                                                 phenyl                         257                                                                                "          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              NHCOCH.sub.3                                                                             OCH.sub.3                                                                            3-methoxy-phenyl                                                                          "                  258                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  259                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  260                                                                                "            "            "          "      "         "                  261                                                                                "            "            "          "    3-methyl-phenyl                                                                           "                  262                                                                                "            "            "        OCH.sub.3                                                                              "         "                  263                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  264                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  265                                                                                "            "            "        OC.sub.2 H.sub.4 OCH.sub.3                                                             "         "                  266                                                                                "            "            "          "    3-methoxy-phenyl                                                                          "                  267                                                                                "            "            "          "    phenyl      "                  268                                                                                "            "            "        OCH.sub.3                                                                              "         "                  269                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  270                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  271                                                                                "            "            "        OCH.sub.3                                                                              "         "                  272                                                                                "          CH.sub.2 CH(CH.sub.3)OCOCH.sub.3                                                             "          "      "         "                  273                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  274                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  275                                                                                "            "            "        OCH.sub.3                                                                              "         "                  276                                                                                "            "            "          "    3-methoxy-carbonyl-                                                                       "                                                                 phenyl                         277                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     3-methoxy-carbonyl-                                                                       "                                                                 phenyl                         278                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    3-methoxy-carbonyl-                                                                       "                                                                 phenyl                         279                                                                                "            "          OCH.sub.3  OCH.sub.3                                                                            3-methoxy-carbonyl-                                                                       "                                                                 phenyl                         280                                                                                "            "            "          "    3-methyl-phenyl                                                                           "                  281                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  282                                                                                "          CH.sub.2 CH(CH.sub.3)OCOCH.sub.3                                                           NHCOCH.sub.3                                                                             OCH.sub.3                                                                            3-methylphenyl                                                                            "                  283                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  284                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         285                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         286                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         287                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         288                                                                                "            "            "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         289                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         290                                                                                "            "          NHCOCH.sub.3                                                                               "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         291                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         292                                                                                "          CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                               "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         293                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         294                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         295                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         296                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         297                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         298                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         299                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         300                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  301                                                                                "            "            "        OCH.sub.3                                                                              "         "                  302                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  303                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  304                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  305                                                                                "            "            "        OCH.sub.3                                                                              "         "                  306                                                                                "            "          NHCOCH.sub.3                                                                               "    3-methylphenyl                                                                            "                  307                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  308                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  309                                                                                "            "            "        OCH.sub.3                                                                              "         "                  310                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  311                                                                                "          CH.sub.2 CH(CH.sub.3)OCOOCH.sub.3                                                            "          "      "         "                  312                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  313                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  314                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  315                                                                                "            "            "        OCH.sub.3                                                                              "         "                  316                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  317                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         318                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         319                                                                                "            "          NHCOCH.sub.3                                                                               "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         320                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         321                                                                                "            "            "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         322                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         323                                                                                "            "            "        OC.sub.2 H.sub.4 OCH.sub.3                                                           4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         324                                                                                "                                                                                         ##STR153##    "        OCH.sub.3                                                                            4-hydroxyphenyl                                                                           "                  325                                                                                "          CH.sub.2 CHCH.sub.2                                                                          "          "      "         "                  326                                                                                "          CH.sub.2 CHCHCl                                                                              "          "      "         "                  327                                                                                "          CH.sub.2 CHCH.sub.2                                                                        NHCOC.sub.2 H.sub.5                                                                        "      "         "                  328                                                                               ##STR154##                                                                                 ##STR155##  NHCOCH.sub.3                                                                             OCH.sub.3                                                                             ##STR156##                                                                               "                  329                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         330                                                                                "            "            "        OCH.sub.2 CH.sub.3                                                                   4-methoxycarbonyl-                                                                        "                                                                 phenyl                         331                                                                                "            "          NHCOCH.sub.3                                                                               "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         332                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         333                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  334                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  335                                                                                "            "          NHCOC.sub.2 H.sub.2                                                                        "      "         "                  336                                                                                "            "            "        OCH.sub.3                                                                              "         "                  337                                                                                "            "            "          "    3-methylphenyl                                                                            "                  338                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  339                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  340                                                                                "            "            "        OCH.sub.3                                                                              "         "                  341                                                                                "            "            "        OC.sub.2 H.sub.4.CH.sub.3                                                            phenyl      "                  342                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  343                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  344                                                                                "            "            "          "      "         "                  345                                                                                "          CH.sub.2 CHCH.sub.2                                                                        NHCOCH.sub.3                                                                             OCH.sub.3                                                                            4-methoxycarbonyl-                                                                      navy blue                                                           phenyl                         346                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         347                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         348                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         349                                                                                "            "            "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         350                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         351                                                                                "            "          NHCOCH.sub.3                                                                               "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         352                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         353                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  354                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  355                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  356                                                                                "            "            "        OCH.sub.3                                                                              "         "                  357                                                                                "            "            "          "    3-methylphenyl                                                                            "                  358                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  359                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  360                                                                                "            "            "        OCH.sub.3                                                                              "         "                  361                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    phenyl      "                  362                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  363                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  364                                                                                "          CH.sub.2 CHCHCl                                                                              "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         365                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methxoycarbonyl-                                                                        "                                                                 phenyl                         366                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         367                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         368                                                                                "          CH.sub.2 CHCHCl                                                                            NHCOCH.sub.3                                                                             OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         369                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         370                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         371                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         372                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  373                                                                                "            "            "        OCH.sub.3                                                                              "         "                  374                                                                                "            "          NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       "         "                  375                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  376                                                                                "            "            "        OCH.sub.3                                                                              "         "                  377                                                                                "          CH.sub.2 CHCHCl                                                                              "          "    3-methylphenyl                                                                            "                  378                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  379                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  380                                                                                "            "            "        OCH.sub.3                                                                              "         "                  381                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  382                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  383                                                                                "            "            "          "    phenyl      "                  384                                                                                "            "            "        OCH.sub.3                                                                              "         "                  385                                                                                "            "          NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       "         "                  386                                                                                "          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         387                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         388                                                                                "            "          NHCOOCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         389                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         390                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         391                                                                                "            "          NHCOCH.sub.3                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                           4-methoxycarbonyl-                                                                        "                                                                 phenyl                         392                                                                                "            "          NHCOCH.sub.3                                                                             OCH.sub.3                                                                            3-methoxyphenyl                                                                           "                  393                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  394                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  395                                                                                "            "            "          "      "         "                  396                                                                                "            "            "          "    3-methylphenyl                                                                            "                  397                                                                                "            "            "        OCH.sub.3                                                                              "         "                  398                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  399                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  400                                                                                "            "            "        OC.sub.2 H.sub.4 OCH.sub.3                                                             "         "                  401                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  402                                                                                "            "            "          "    phenyl      "                  403                                                                                "            "            "        OCH.sub.3                                                                              "         "                  404                                                                                "            "          NHCOOCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       "         "                  405                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  406                                                                                "            "            "        OCH.sub.3                                                                              "         "                  407                                                                                "          CH.sub.2 CH(CH.sub.3)OCOCH.sub.3                                                             "          "      "         "                  408                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  409                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  410                                                                                "            "            "        OCH.sub.3                                                                              "         "                  411                                                                                "            "            "          "    3-methoxycarbonyl-                                                                        "                                                                 phenyl                         412                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     3-methoxycarbonyl-                                                                        "                                                                 phenyl                         413                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    3-methoxycarbonyl-                                                                        "                                                                 phenyl                         414                                                                                "            "            "        OCH.sub.3                                                                            3-methoxycarbonyl-                                                                        "                                                                 phenyl                         415                                                                                "            "            "          "    3-methylphenyl                                                                            "                  416                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  417                                                                                "          CH.sub.2 CH(CH.sub.3)OCOCH.sub.3                                                           NHCOCH.sub.3                                                                             OCH.sub.3                                                                            3-methylphenyl                                                                            "                  418                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  419                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         420                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         421                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         422                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         423                                                                                "            "            "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         424                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         425                                                                                "            "          NHCOCH.sub.3                                                                               "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         426                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         427                                                                                "          CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                               "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         428                                                                                "            "            "        OCH.sub.3                                                                            4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         429                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         430                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         431                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         432                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         433                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         434                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         435                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  436                                                                                "            "            "        OCH.sub.3                                                                              "         "                  437                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  438                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  439                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  440                                                                                "            "            "        OCH.sub.3                                                                              "         "                  441                                                                                "          CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                             NHCOCH.sub.3                                                                               "    3-methylphenyl                                                                            "                  442                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  443                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                        "      "         "                  444                                                                                "            "            "        OCH.sub.3                                                                              "         "                  445                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  446                                                                                "          CH.sub.2 CH(CH.sub.3)OCOOCH.sub.3                                                            "          "      "         "                  447                                                                                "            "          NHCOCH.sub.3                                                                               "      "         "                  448                                                                                "            "            "        OC.sub.2 H.sub.5                                                                       "         "                  449                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  450                                                                                "            "            "        OCH.sub.3                                                                              "         "                  451                                                                                "            "          NHCOOCH.sub.3                                                                              "      "         "                  452                                                                                "            "            "          "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         453                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-methoxycarbonyl-                                                                        "                                                                 phenyl                         454                                                                                "            "          NHCOCH.sub.3                                                                               "    4-methoxycarbonyl-                                                                        "                                                                 phenyl                         455                                                                                "            "            "        OCH.sub.3                                                                            4-methoxycarbonyl-                                                                        "                                                                 phenyl                         456                                                                                "            "            "          "    4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         457                                                                                "            "            "        OC.sub.2 H.sub.5                                                                     4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         458                                                                                "            "            "        OC.sub.2 H.sub.4 OCH.sub.3                                                           4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         459                                                                                "                                                                                         ##STR157##    "        OCH.sub.3                                                                            4-hydroxyphenyl                                                                           "                  460                                                                                "          CH.sub.2 CHCH.sub.2                                                                          "          "      "         "                  461                                                                                "          CH.sub.2 CHCHCl                                                                              "          "      "         "                  462                                                                                "          CH.sub.2 CHCH.sub.2                                                                        NHCOC.sub.2 H.sub.5                                                                        "      "         "                  463                                                                               ##STR158##    "          NHCOCH.sub.3                                                                               "    4-oxycarbonyphenyl                                                                        "                  464                                                                                "            "            "          "    3-methoxyphenyl                                                                           "                  465                                                                               ##STR159##  CH.sub.2 CH.sub.2                                                                          NHCOCH.sub.3                                                                             H      phenyl      "                  466                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "         "                  467                                                                                "          CH(CH.sub.3)CH.sub.3                                                                         "        H        "         "                  468                                                                                "            "          NHCOCH.sub.3                                                                             H        "         "                  469                                                                                "                                                                                         ##STR160##    "        H        "         "                  470                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "         "                  471                                                                                "          CH(CH.sub.3)C.sub.4 H.sub.9 -n                                                             NHCOCH.sub.3                                                                             H        "         "                  472                                                                                "            "            "        H      3-methoxyphenyl                                                                           "                  473                                                                                "          CHCH.sub.3     "        H        "         "                  474                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "         "                  475                                                                                "          CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                   "        H        "         "                  476                                                                                "            "          NHCOCH.sub.3                                                                             H        "         "                  477                                                                                "            "            "        H      3-methylphenyl                                                                            "                  478                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "         "                  479                                                                                "          CH.sub.2 CH.sub.3                                                                            "        H        "         "                  480                                                                                "                                                                                         ##STR161##    "        H        "         "                  481                                                                                "          CH.sub.2 CH.sub.2 CH.sub.3                                                                 NHCOCH.sub.3                                                                             H        "         "                  482                                                                                "            "            "        H      3-methoxyphenyl                                                                           "                  483                                                                                "          CH.sub.2 CH.sub.3                                                                            "        H      4-methoxyphenyl                                                                           "                  484                                                                                "            "            "        H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         485                                                                                "            "          NHCOCH.sub.2 CH.sub.3                                                                    H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         486                                                                                "                                                                                         ##STR162##  NHCOCH.sub.3                                                                             H                                                                                     ##STR163##                                                                               "                  487                                                                                "          CH.sub.2 CH.sub.3                                                                            "        H      4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         488                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H      4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         489                                                                                "          CH.sub.2 CHCH.sub.2                                                                        NHCOCH.sub.3                                                                             H      phenyl      "                  490                                                                                "            "            "        H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         491                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         492                                                                                "            "            "        H      3-methoxyphenyl                                                                           "                  493                                                                                "            "          NHCOCH.sub.3                                                                             H        "         "                  494                                                                                "            "            "        H      3-methylphenyl                                                                            "                  495                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "         "                  496                                                                                "            "          NHCOCH.sub.3                                                                             H      4-methoxyphenyl                                                                           "                  497                                                                                "                                                                                         ##STR164##    "        H      3-methoxyphenyl                                                                          ##STR165##          498                                                                                "            "            "        H      phenyl    bluish                                                                        violet               499                                                                                "            "          NHCOOCH.sub.3                                                                            H        "       bluish                                                                        violet               500                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "       bluish                                                                        violet               501                                                                                "          CH.sub.2 CH.sub.2 COOCH.sub.3                                                              NHCOCH.sub.3                                                                             H      3-methyoxyphenyl                                                                        bluish                                                                        violet               502                                                                                "            "            "        H      3-methylphenyl                                                                          bluish                                                                        violet               503                                                                                "          CH.sub.2 CH.sub.2 COOCH.sub.3                                                                "        H        "       bluish                                                                        violet               504                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               505                                                                                "          CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.3                                                       "        H        "       bluish                                                                        violet               506                                                                                "            "            "        H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               507                                                                                "          CH.sub.2 C.sub.6 H.sub.5                                                                     "        H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               508                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               509                                                                                "          CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                            "        H        "       bluish                                                                        violet               510                                                                                "            "            "        H      phenyl    bluish                                                                        violet               511                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H        "       bluish                                                                        violet               512                                                                                "          CH.sub.2 CHCHCl                                                                            NHCOCH.sub.3                                                                             H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               513                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               514                                                                                "          CH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                   "        H      phenyl    bluish                                                                        violet               515                                                                                "            "            "        H        "       bluish                                                                        violet               516                                                                                "          CH.sub.2 CH.sub.3                                                                            "        H        "       bluish                                                                        violet               517                                                                                "            "            "        H      4-methxoycarbonyl-                                                                      bluish                                                              phenyl    violet               518                                                                                "            "          NHCOC.sub.2 H.sub.5                                                                      H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               519                                                                                "                                                                                         ##STR166##  NHCOCH.sub.3                                                                             H                                                                                     ##STR167##                                                                              ##STR168##          520                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               521                                                                                "          CH.sub.2 CH.sub.3                                                                            "        H        "       bluish                                                                        violet               522                                                                                "            "          NHCOOCH.sub.3                                                                            H        "       bluish                                                                        violet               523                                                                                "            "          NHCOCHCH.sub.2                                                                           H        "       bluish                                                                        violet               524                                                                                "            "            "        H      phenyl    bluish                                                                        violet               525                                                                                "            "            "        H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               526                                                                                "            "          NHCOCH.sub.2 OCH.sub.3                                                                   H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               527                                                                                "            "            "        H      phenyl    bluish                                                                        violet               528                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               529                                                                                "            "            "        H      4-methoxyphenyl                                                                         bluish                                                                        violet               530                                                                                "            "            "        H      4-ethoxyphenyl                                                                          bluish                                                                        violet               531                                                                                "            "            "        H        "       bluish                                                                        violet               532                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               533                                                                                "            "            "        H      phenyl    bluish                                                                        violet               534                                                                                "          CH.sub.2 CH.sub.3                                                                          NHCOCHCH.sub.2                                                                           H        "       bluish                                                                        violet               535                                                                                "            "            "        H      4-methoxycarbonyl-                                                                      bluish                                                              phenyl    violet               536                                                                                "            "            "        H      3-methoxyphenyl                                                                         bluish                                                                        violet               537                                                                                "            "            "        H        "       bluish                                                                        violet               538                                                                                "            "          NHCOCH.sub.3                                                                             H      4-methylphenyl                                                                          bluish                                                                        violet               539                                                                                "            "            "        H      2-methylphenyl                                                                          bluish                                                                        violet               540                                                                                "            "            "        H      2-methoxyphenyl                                                                         bluish                                                                        violet               541                                                                                "                                                                                         ##STR169##    "        H        "                                                                                      ##STR170##          542                                                                                "          CH.sub.2 CHCH.sub.2                                                                          "        H        "       bluish                                                                        violet               543                                                                                "          CH.sub.2 CHCHCl                                                                              "        H        "       bluish                                                                        violet               544                                                                                "            "            "        H      2-methylphenyl                                                                          bluish                                                                        violet               545                                                                                "                                                                                         ##STR171##    "        H        "                                                                                      ##STR172##          546                                                                                "          CH.sub.2 CHCH.sub.2                                                                          "        H        "       bluish                                                                        violet               547                                                                                "            "            "        H      2-methoxyphenyl                                                                         bluish                                                                        violet               548                                                                                "            "                                                                                         ##STR173##                                                                              H                                                                                     ##STR174##                                                                              ##STR175##          549                                                                                "                                                                                         ##STR176##    "        H                                                                                     ##STR177##                                                                              ##STR178##          550                                                                                "            "                                                                                         ##STR179##                                                                              H                                                                                     ##STR180##                                                                              ##STR181##          551                                                                               ##STR182##    "            "        H                                                                                     ##STR183##                                                                              ##STR184##          552                                                                               ##STR185##  CH.sub.3     H          H                                                                                     ##STR186##                                                                              ##STR187##          553                                                                               ##STR188##  CH.sub.3     H          H                                                                                     ##STR189##                                                                              ##STR190##          554                                                                               ##STR191##  CH.sub.3     H          H                                                                                     ##STR192##                                                                              ##STR193##          555                                                                               ##STR194##                                                                                 ##STR195##  NHCOCH.sub.3                                                                             H      3-methoxyphenyl                                                                          ##STR196##          556                                                                               ##STR197##    "            "        H        "                                                                                      ##STR198##          557                                                                                "                                                                                         ##STR199##  NHCOCHCH.sub.2                                                                           H                                                                                     ##STR200##                                                                              ##STR201##          558                                                                               ##STR202##    "          NHSO.sub.2 CH.sub.3                                                                      H                                                                                     ##STR203##                                                                              ##STR204##          559                                                                               ##STR205##                                                                                 ##STR206##    "        H                                                                                     ##STR207##                                                                              ##STR208##          560                                                                               ##STR209##  CH.sub.2 CH.sub.3                                                                          H          H                                                                                     ##STR210##                                                                              ##STR211##          561                                                                               ##STR212##  CH.sub.2 CH.sub.2 COCH.sub.3                                                               NHCOCH.sub.3                                                                             H                                                                                     ##STR213##                                                                              ##STR214##          562                                                                                "          CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.3                                                       "        H      4-methoxycarbonyl-                                                                      reddish-                                                            phenyl    violet               563                                                                               ##STR215##  CH.sub.2 CH.sub.3                                                                            "        H      phenyl                                                                                   ##STR216##          564                                                                               ##STR217##    "            "        H        "                                                                                      ##STR218##          565                                                                                "          CHC.sub.4 H.sub.9                                                                            "        H        "       blue                 566                                                                                "            "            "        H      3-methoxyphenyl                                                                           "                  567                                                                               ##STR219##    "            "        H        "         "                  568                                                                                "          CH.sub.2 CH.sub.3                                                                          NHCOCH.sub.2 CH.sub.3                                                                    H        "         "                  569                                                                               ##STR220##  CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              H          H                                                                                     ##STR221##                                                                             bluish red           570                                                                                "          CH.sub.2 CH.sub.2 OCOCH.sub.2 CH.sub.3                                                     H          H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         571                                                                                "          CH.sub.2 CH.sub.2 OCOOCH.sub.3                                                             H          H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         572                                                                                "          CH.sub.2 CH(CH.sub.3)COOCH.sub.3                                                           H          H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         573                                                                                "          CH.sub.2 CH(CH.sub.3)COOCH.sub.3                                                           H          H      4-methoxycarbonyl-                                                                        "                                                                 phenyl                         574                                                                                "            "          H          H      4-ethoxycarbonyl-                                                                         "                                                                 phenyl                         575                                                                                "                                                                                         ##STR222##  H          H                                                                                     ##STR223##                                                                               "                  __________________________________________________________________________

Application Example

20 parts of the dyestuff of Example 1 in the form of a wet presscake arewet milled with 80 parts of a commercially available dispersingligninsulphonate dispersing agent and then are dried to a powder.

3.0 parts of the resulting dyeing preparation are added to 2000 parts ofdemineralized water at 70° C., containing 40 parts of ammonium sulphateto form a dyebath in a dyeing machine. With an 85% aqueous formic acidsolution, the pH is brought to 5.

100 parts of a precleaned polyester fiber material is added to thedyebath, the dyeing apparatus is closed, and the bath is heated to 130°C. over 20 minutes. Dyeing is carded out at this temperature for afurther 40 minutes. After cooling, the polyester fiber material isremoved from the bath, washed, soaped and reductively cleaned withsodium hydrosulphite.

A clear brilliant rubine-red dyeing having good thermomigration, washfastness, rubbing fastness, light fastness and sublimation fastnessproperties results.

The Application Example can be repeated using 20 parts of the dyestuffof any one of Examples 2-575 in place of that of Example 1.

What is claimed is:
 1. A compound of the formula ##STR224## wherein D is##STR225## wherein R₂₀ is hydrogen, C₁₋₄ alkyl, halo, (C₁₋₄alkoxy)carbonyl, cyano or nitro,R₂₁ is halo, C₁₋₄ alkyl, nitro,phenylazo or phenylazo the phenyl group of which is substituted by 1 to4 substituents each of which is independently C₁₋₄ alkyl, nitro, halo orC₁₋₄ alkoxy, R₂₂ is hydrogen, halo, cyano or (C₁₋₄ alkoxy)carbonyl, R₂₃is formyl, cyano, --CH═N--O--C₁₋₄ alkyl or --CH═C(CN)R_(25a), whereinR_(25a) is cyano or (C₁₋₄ alkoxy)carbonyl, and R₂₄ is (C₁₋₄alkoxy)carbonyl, nitro or cyano, R_(1a) is phenyl or phenyl substitutedby 1 to 4 substituents each of which is independently halo, C₁₋₄ alkyl,C₁₋₄ alkoxy, trifluoromethyl, hydroxy, nitro, formyl, cyano, --SCN,(C₁₋₄ alkyl)carbonyl, (C₁₋₄ alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonyl,(C₁₋₄ alkyl)carbonyloxy, carbamoyl, (C₁₋₂ alkoxy)(C₂₋₃ alkoxy)carbonylor phenyl, R₂ is hydrogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, halo(C₂₋₆ alkenyl),C₃₋₈ alkynyl, benzyl, phenylethyl, phenylpropyl, hydroxy(C₁₋₆ alkyl),(C₁₋₄ alkoxy)C₁₋₄ alkyl, (C₁₋₄ alkoxy)carbonyl(C₁₋₄ alkyl), (C₁₋₄alkyl)carbonyloxy(C₁₋₄ alkyl) or (C₁₋₄ alkoxy)carbonyloxy(C₁₋₄ alkyl),with the proviso that R₂ may be hydrogen only when D is a heterocyclicgroup, 2,4-dinitrophenyl or 2,4-dinitrophenyl having a substituent inthe 6-position, and R₃ is hydrogen or C₁₋₄ alkyl, wherein each halo isindependently fluoro, chloro, bromo or iodo.
 2. A compound according toclaim 1 wherein R₂₁ is halo, C₁₋₄ alkyl, nitro or phenylazo.
 3. Acompound according to claim 2 wherein D is 2-cyano-4-nitrophenyl,2,4-dinitro-6-bromophenyl, 2,6-dichloro-4-nitrophenyl or2,4-dinitro-6-chlorophenyl.
 4. A compound according to claim2whereinR_(1a) is ##STR226## wherein each R_(26a) is independentlyhydrogen, fluoro, chloro, (C₁₋₂ alkoxy)carbonyl, methyl, methoxy orethoxy, R_(27a) is hydrogen, fluoro, chloro, bromo, methyl, methoxy,ethoxy, (C₁₋₂ alkoxy)carbonyl or phenyl, and R₂₈ is hydrogen, methyl,methoxy or ethoxy, R₂ is methyl, ethyl, allyl, 2-methylallyl,chloroallyl, propynyl, (C₁₋₂ alkyl)carbonyloxyethyl or (C₁₋₂alkoxy)carbonyloxyethyl, and R₃ is hydrogen or methyl.
 5. A compoundaccording to claim 4 wherein at least one R_(26a), R_(27a) or R₂₈ ishydrogen.
 6. A compound according to claim 5 wherein at least two of theR_(26a) 's, R_(27a) and R₂₈ are hydrogen.
 7. A compound according toclaim 6 wherein D is 2-cyano-4-nitrophenyl, 2,4-dinitro-6-bromophenyl,2,6-dichloro-4-nitrophenyl or 2,4-dinitro-6-chlorophenyl.
 8. A compoundaccording to claim 1whereinR_(1a) is ##STR227## wherein each R_(26a) isindependently hydrogen, fluoro, chloro, (C₁₋₂ alkoxy)carbonyl, methyl,methoxy or ethoxy, R_(27a) is hydrogen, fluoro, chloro, bromo, methyl,methoxy, ethoxy, (C₁₋₂ alkoxy)carbonyl or phenyl, and R₂₈ is hydrogen,methyl, methoxy or ethoxy.
 9. A compound according to claim 8 wherein atleast one R_(26a), R_(27a) or R₂₈ is hydrogen.
 10. A compound accordingto claim 9 wherein at least two of the R_(26a) ', R_(27a) and R₂₈ arehydrogen.
 11. A compound according to claim 1 whereinR₂ is methyl,ethyl, allyl, 2-methylallyl, chloroallyl, propynyl, (C₁₋₂alkyl)carbonyloxyethyl or (C₁₋₂ alkoxy)carbonyloxyethyl.
 12. A compoundaccording to claim 1 wherein R₃ is hydrogen or methyl.
 13. A compoundaccording to claim 1 having the formula ##STR228## wherein R₅₀ is C₁₋₄alkyl, andn is 0 or
 1. 14. The compound according to claim 13 having theformula ##STR229##
 15. The compound according to claim 13 having theformula ##STR230##
 16. A compound according to claim 1 having theformula ##STR231## wherein R₅₀ is C₁₋₄ alkyl, andn is 0 or
 1. 17. Thecompound according to claim 16 having the formula ##STR232##
 18. Thecompound according to claim 13 having the formula ##STR233##
 19. Acompound according to claim 1 having the formula ##STR234## wherein R₃is hydrogen or C₁₋₄ alkyl,R₅₁ is nitro or cyano, R₅₂ is chloro, bromo orcyano, R₅₃ is C₁₋₆ alkyl, C₂₋₆ alkenyl, halo(C₂₋₆ alkenyl), C₃₋₈alkynyl, benzyl, phenylethyl, phenylpropyl, hydroxy(C₁₋₆ alkyl), (C₁₋₄alkoxy)C₁₋₄ alkyl, (C₁₋₄ alkoxy)carbonyl(C₁₋₄ alkyl), (C₁₋₄alkyl)carbonyloxy(C₁₋₄ alkyl) or (C₁₋₄ alkoxy)carbonyloxy(C₁₋₄ alkyl),and R₅₄ is C₁₋₄ alkyl, C₁₋₄ alkoxy, (C₁₋₄ alkoxy)carbonyl or (C₁₋₄alkyl)carbonyl.
 20. The compound according to claim 1 having the formula##STR235##
 21. A substrate to which a compound according to claim 1 wasapplied.
 22. A substrate according to claim 21 which is a textilematerial comprising natural, semi-synthetic or fully synthetichydrophobic, high molecular weight organic material.